Diethyl Ether → HCID 68133257, compound

Participants

Reaction Steps

To a solution of 3 moles of lithium diisopropylamide in 3 liters ether is added 3 moles of β-picoline. After 1/2 hour, a solution of 1 mole methyl anisate in ether is added dropwise. After 1 hour under reflux, the mixture is cooled and decomposed with water. After all the lithium has dissolved, the layers are separated. The organics are washed with water, dried (magnesium sulfate) and distilled. The product is collected at 155°-165°C at 0.3 mm Hg and recrystallized from benzene-pet ether to yield 88 g (39%) 4-methoxy-α-(3-pyridyl)-acetophenone. [Miller, Osuch, Goldberg, and Levine, JACS, 78, 674 (1956) and Raynolds and Levine, JACS, 82, 472 (1960)].

Provenance & Evidence